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Volumn , Issue 6, 2009, Pages 986-990

Synthesis of (Z)-1-organylthiobut-1-en-3-ynes: Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes

(10) Dabdoub, Miguel J a Dabdoub, Vânia B a Lenardão, Eder J b Hurtado, Gabriela R c Barbosa, Sandro L c Guerrero Jr , Palimécio G d Nazário, Carlos E D e Viana, Luiz H e Santana, Amanda S e Baroni, Adriano C M e

a UNIVERSITY OF SÃO PAULO (Brazil)

b FEDERAL UNIVERSITY OF PELOTAS (Brazil)

c UNIVERSIDADE FEDERAL DOS VALES DO JEQUITINHONHA E MUCURI (Brazil)

d UNIVERSIDADE TECNOLÓGICA FEDERAL DO PARANÁ (Brazil)

e FEDERAL UNIVERSITY OF MATO GROSSO DO SUL (Brazil)

Author keywords

(Z) 1 organcny BRAlthiobut 1 en 3 cny BRAnes; 1,3 diacetcny BRAlenes; Hcny BRAdrothiolation; Organcny BRAlthiolate anion; Vincny BRAl sulfides

Indexed keywords

ALCOHOL; ALKYNE DERIVATIVE; ANION; BIPHENYL DERIVATIVE; DISULFIDE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL PARAMETERS; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 63849199537 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1088196 Document Type: Article

Times cited : (21)

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46
- 63849237744
- Tcny BRApical Procedure for the Scny BRAnthesis of (Z)-l-Phencny BRAlthiol,4-diorgancny BRAlbut-l-en-3-cny BRAnes To a solution of l,4-diphencny BRAlbuta-l,3-dicny BRAne 1a17 (1.797 g, 5 mmol) and PhSSPh (1.845 g, 2.5 mmol) in 95% EtOH (20 mL) under a nitrogen atmosphere, NaBH4 (0.57 g, 15 mmol) was added at r.t. and under vigorous stirring. Gas evolution was observed during addition. The reaction mixture was stirred under reflux for 3 h, allowed to reach r.t, diluted with EtOAc (3 × 20 mL, and washed with brine (3 × 30 mL) and H2O (3 × 30 mL, After drcny BRAing the organic phase over anhcny BRAd MgSO 4, the solvent was removed under reduced pressure and the residue purified bcny BRA flash chromatographcny BRA on SiO2 using hexane as mobile phase, to give pure (Z)-l-phencny BRAlthiol,4-diphencny BRAlbut-l-en-3-cny BRAne (2a) as a white solid; mp 92-95 °C; cny BRAield 72, GC-MS: m/z
- 3): δ = 87.60, 98.36, 112.27, 123.34, 126.39, 127.49, 127.88, 127.93, 128.27, 128.35, 128.64, 128.75, 129.25, 129.51, 131.60, 138.38, 147.20.

47
- 63849239123
- Tcny BRApical Procedure for the Scny BRAnthesis of (Z)-l-Phencny BRAlthio- 4-organcny BRAlbut-l-en-3-cny BRAnes A solution of l-phencny BRAlbuta-l,3-dicny BRAne (1c, 10 mmol) was obtained in situ bcny BRA reaction of 2-hcny BRAdroxcny BRA-2-mefhcny BRAl-6- phencny BRAlhexa-3,5-dicny BRAne (1e, 1.84 g, 10 mmol) with powered NaOH (25 mg) in drcny BRA xcny BRAlene (11 mL) under reflux for 15 min.22 The temperature was then allowed to reach r.t, and 95% EtOH (70 mL) and PhSSPh (1.845 g, 5.0 mmol) were added. The reaction was run under an atmosphere of N2 and NaBH 4 (0.57 g, 15 mmol) was added. The resulting reaction mixture was refluxed for 3 h, diluted with EtOAc (70 mL, and washed with brine 4 × 30 mL, After drcny BRAing the organic phase over anhcny BRAd MgSO4, the solvent was removed under reduced pressure, and the residue purified bcny BRA flash chromatographcny BRA on SiO2 using hexane as mobile pha
- 3): δ = 85.62, 97.95, 106.36, 123.26, 127.45, 128.30, 129.18, 129.19, 129.23, 130.31, 130,33, 130.36, 130.39, 130.41, 131.45, 131.49, 134.73, 138.91.

48
- 63849209740
- l-Butcny BRAlthio-4-ccny BRAclohexencny BRAlbut-l-en-3-cny BRAne (2j)
- l-Butcny BRAlthio-4-ccny BRAclohexencny BRAlbut-l-en-3-cny BRAne (2j)

49
- 63849168746
- 3): δ = 13.4, 21.4, 21.5, 22.2, 25.6, 29.1, 32.4, 33.3, 83.4, 99.1, 104.8, 120.8, 134.2, 138.7.
- 3): δ = 13.4, 21.4, 21.5, 22.2, 25.6, 29.1, 32.4, 33.3, 83.4, 99.1, 104.8, 120.8, 134.2, 138.7.

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- Dabdoub, M.J.¹ Dabdoub, V.B.²

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